From left: Dee Wells, Rick Kosow, and Peter Gold are the organizers of Boston Sneaker Jam, billed as the largest sneakerhead convention in New England.

By Ethan Gilsdorf
Globe Correspondent
October 17, 2014

Dee Wells remembers how his sneaker obsession began. It was 1983. “Mesmerized,” he recalls, by his parents’ Adidas Stan Smith and Rod Laver shoes, he saved up money from odd jobs. His first pair: Puma Clydes. He was 10 years old.

Before long, he began paying $50, $65, $100 for a pair, even sending money orders to cousins in Chicago and New York to buy him makes and models he could not find where he grew up, on St. John in the US Virgin Islands. “People thought I was crazy to spend that amount of money on ‘tennis shoes’ as they were called,” says Wells, 41, who is based in Worcester.

Wells kept buying. He went on to found the sneaker culture website Obsessive Sneaker Disorder.
His collection of “kicks” now numbers some 700 pairs.

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Wells is far from alone. The subculture of largely teen and 20-something sneaker fans, known as “sneakerheads,” has mushroomed. Dozens of sneaker publications and websites with names like Nicekicks and Sole Collector have sprung up, tracking industry news and providing forums for networking.

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Each year, more US cities host sneaker events where the faithful buy, sell, and trade pairs. A traveling event called Dunkxchange has made stops from Honolulu to Miami and overseas. Locally, the area has twice hosted an event called Boston Got Sole, as well as New England Sneaker Social, which show organizers say attracted 3,000 to Gillette Stadium in April.

To celebrate the wider heart and soul of sneakerhead culture — from sports fans to rap fashionistas, skateboarders to street artists — Wells has joined forces with three other local sneaker aficionados and promoters to throw
Boston Sneaker Jam. The two-day convention this weekend at the Seaport World Trade Center is expected to be the largest such gathering ever in the region and is aiming for a vibe different from the standard sneaker event.

Gretchen Ertl for The Boston Globe

Clockwise from top left: original Nike Cortez from 1982, a Nike Air Force 180 sneaker that has been painted by Boston artist Josh Wisdum, a Converse Wade 1 sneaker from 2006, and an Air Jordan 5 lifestyle sneaker from 1990.

The idea began with Richard Kosow, creator of Boston’s Sneaker Museum. Kosow had been talking about a big Boston sneaker convention “for a long time,” says Peter Gold, Sneaker Jam cofounder and a veteran producer of such events as MixFest on Boston Common.

During a drive around a year ago to a New York sneaker event, Kosow finally convinced Gold to make it happen. “I said, ‘If New York can do it, we can do it better,’ ” says Gold. He and Kosow approached Jim Talbot, a pop-culture collector who runs
Boston Comic Con — an event with the same format, different geekery.

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Then, at this year’s SneakerSocial, Kosow met Wells, a sneaker-event veteran who knew the culture and was brought on as the fourth team member. Wells remembers thinking that when he got to know Kosow, what brought them together was “that appreciation of sneakers as wearable art.”

The four shared the same vision: what Gold calls “not just a sneaker community event, but a community sneaker event.”

Industry observers say that the rapid growth of conventions has mirrored that of the culture.

“There is no question that the level of trading, buying, and reselling sneakers, all that rolled into one, has accelerated in the last five years or so,” says Matt Powell, a Scarborough, Maine-based “sneakerologist” and analyst for the sneaker research site SportsOneSource. “Because of that, it’s accelerated physical events like Sneaker Jam.”

Sneaker Jam organizers believe the event will be a huge success. Jemayne King, author of “Sole Food: Digestible Sneaker Culture,” and a faculty member at Johnson C. Smith University in Charlotte, N.C., agrees that the Jam has a decent shot at drawing record crowds.

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Other gatherings typically attract hundreds or a couple thousand attendees and run just a few hours over a single day, focusing almost exclusively on selling shoes. That Sneaker Jam will go seven to eight hours a day over two days and embraces the sneaker’s many tendrils and influences is “a harbinger of the culture,” King says. “Like any subculture, you have the practitioners of the culture, but then it goes pop. And this has definitely gone pop.”

Besides perusing mountains of boxes of sneakers and racks of urban apparel like hats and T-shirts, visitors can also check out a street-art gallery (including work by students from Boston Arts Academy), demos by pro skateboarders, and a sneaker fashion show. For music fans, there will be an ongoing schedule of performances by artists such as Sean Brown, King Los, and Edo G, and several DJs including DJ Pup Dawg. During a “Sneaker Stories” program, attendees will be invited to spin their own yarns about shoes.

Attendees also will get a sampling of Kosow’s not-yet-public Sneaker Museum. Kosow will display about 40 pairs, including his collection of original Air Jordans from 1985 to 1997, and his Converse Chuck Taylor artist series sneakers featuring the Beatles and the Who.

While the exhibits and performances are a plus, for many the focus will remain firmly on the buying-selling-trading area, where sneakerheads can rent tables to display new and unworn (a.k.a. deadstock) sneakers no longer in stock at retail stores — shoes that often sell for many times their retail price. The atmosphere can resemble “being on the floor of the stock exchange,” said Gold. “You see people who are shouting and yelling and raising their hands.”

“If you don’t like sneakers, then you won’t understand why people like them,’’ says Sam Bebergal, 13, of Cambridge, whose nascent sneaker collection numbers about a dozen pairs. Bebergal, who plans to attend this weekend, says he’s not looking for any specific shoe but he’s “bringing money” and will “have my eye out.”

Attendees with an interest in the industry can rub shoulders with shoe professionals. Boston native Greg Selkoe, chief executive of the streetwear company Karmaloop, is speaking on “Starting a Company From Scratch,” and D’Wayne Edwards, founder of Pensole Footwear Design Academy, is giving a talk called “Finding + Designing Your Sole.” Another panel promises this saga: “Coming of Age: How the Sneaker Culture Has Grown Up.”

And how it has grown since the days when Michael Jordan ruled the basketball court. His line of Air Jordans jump-started the phenomenon of designer sneakers worn by athletes. Starry-eyed youth wanted them, too. “As the athletes got more involved, they had a bigger voice in the design aspect, and the materials, the colors,” says Wells.

In 2013, the Air Jordan brand racked up $2.7 billion in sales for Nike, and that figure thus far in 2014 has risen another 15 percent. Overall, basketball sneakers, which are the focus of most collectors, account for $4.5 billion of the $21 billion retail athletic shoe business.

Add to that the sneaker resale market. Savvy sneaker companies release a limited number of a particular make, model and “colorway” (unique color). The gap between supply and demand has created a lucrative resale “aftermarket” — online, in consignment stories, and in person at conventions like the Jam — expected to generate as much as $1 billion over the next year, according to Campless.com, a sneakerhead data site. An in-demand sneaker like the Kanye West-brandedNike Air Yeezy 2 Red October retailed for $250 earlier this year, but resells for around $3,000. Some sneakerheads can make a good living buying and selling sneakers.

With all the commerce involved, events like Sneaker Jam also find themselves situated at the center of a hot debate: whether rarer models should be resold for massive profit. The diehards have “created this aura for shoes,” says Nick Urciuolo, CEO of Mass Apparel, an urban clothier and accessory shop in Allston that will be at the Jam. “They’re not shoes anymore; they’re collectors’ items. It’s gotten to the point where if you wear a rare pair of Jordans, people will get mad at you.”

As for Kosow, he hopes the gathering will teach younger sneaker fans “to reconnect with passion that I once felt when it was a burgeoning industry.” Browsing through his collection is a direct link to his childhood. “When I was a shy person, [sneakers] helped me bridge the gap to other people. I’d have something in common with them.” Indeed, he will likely run into some kindred spirits this weekend.